We’re having a conversation at work that’s got my mind churning. The context is this: every two weeks, our leadership team puts together an update about the support division we lead. The audience is the entire company. And we need to get better at our updates. Right now, the raw inputs we write wouldn’t always make sense to someone outside of our area, or the metrics we write about don’t roll up into the high level metrics we’re trying to influence, or we’re including work that would make others wonder, “Why should I care?”

As our boss told us when giving us this feedback, the quality of how we write about our work reflects the quality of how we think about our work. Beyond just the words we choose, or how we string them together, editorial judgment matters. It matters a lot what we choose to highlight.

This is what I’ve been turning over in my mind. Can judgment be learned? When I say editorial judgment, I don’t mean just fixing grammatical errors and making micro edits, I mean editing at the level of choice: picking the right story to tell.

I listened to an excellent interview with Annie Liebowitz the other day. Liebowitz deflected complements about being an excellent photographer and said instead she’s an excellent editor. I thought this was interesting. She is not afraid to take thousands and thousands of photographs and then weed through them to find The One. She’s not afraid to throw all the rest in the bin. Her interest is not in the input of all the work she did to get that one photo, all the lights she set up or the backdrop she selected or how she got her subject comfortable — we don’t see photographs of all those things. All we see is the One shot of John Lennon and Yoko Ono or a pregnant Demi Moore.

The thing I keep circling around is that in order to reach that level of excellence, you must achieve detachment. Any person who’s ever shown any interest in writing has heard the phrase “Kill your darlings.” In order to edit, you have to kill your ego. You have to look at the work objectively. In the case of our work updates, we can’t be attached to “but we did this cool thing” or “but we had this success here” or “but we’re working so hard.” Instead we have to think about, What are we trying to achieve, how are we doing towards that goal, and what do we need to change to get there if we’re not there yet.

Some people seem to do this with ease. They see straight to the heart of an issue and think clearly and write clearly about it. I have to work really hard at it. I tend to cling to my darlings. And when I do, my judgment is clouded, both editorial and otherwise: I’m not thinking clearly about what we’re doing in a way that I can tell a succinct story to someone who has no idea what we do or why it matters. I’m thinking about the lighting and the camera settings instead of the actual developed photograph.

The reason I keep turning this over in my head is because I fear that editorial judgment, which reflects judgment overall about how I think about our work, cannot be learned. But I really want to master it. Then I remember my original chat with our CEO when I was hired. He asked if I thought good customer support could be learned. I answered that I think anything can be learned if you care enough to learn it.